SYNTHESIS OF THE DISACCHARIDES METHYL 4-O-(2' 3'-O-SULFO-BETA-D-GLUCOPYRANOSYLURONIC ACID)-2-AMINO-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE DISODIUMSALTS, RELATED TO HEPARIN BIOSYNTHESIS/

Authors
CIPOLLA L NICOTRA F LAY L LINDAHL U PANZA L RUSSO G
Citation
L. Cipolla et al., SYNTHESIS OF THE DISACCHARIDES METHYL 4-O-(2' 3'-O-SULFO-BETA-D-GLUCOPYRANOSYLURONIC ACID)-2-AMINO-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE DISODIUMSALTS, RELATED TO HEPARIN BIOSYNTHESIS/, Glycoconjugate journal, 13(6), 1996, pp. 995-1003
Citations number
23
Categorie Soggetti
Biology
Journal title
Glycoconjugate journal → ACNP
ISSN journal
02820080
Volume
13
Issue
6
Year of publication
1996
Pages
995 - 1003
Database
ISI
SICI code
0282-0080(1996)13:6<995:SOTDM4>2.0.ZU;2-7
Abstract
The synthesis of the disaccharides methyl 4-O-(2'/3'-O-sulfo-beta-D-gl ucopyranosyluronic acid)-2-amino-2-deoxy-alpha-D-glucopyranoside 3 and 4 as disodium salts is described. Allyl 4,6-O-benzylidene-alpha-D-glu copyranoside 6 was converted to trichloroacetimidate 20. Glycosylation of 20 with 5 promoted by BF3 . OEt(2) gave disaccharide 21. Deacetyla tion of 21 followed by monoacetylation of the resultant diol 22 afford ed the two monoacetylated disaccharides 23 and 24. Sulfation and depro tection of each disaccharide gave the desired sulfated compounds 3 and 4.